During an emotional scene in the film, Miles talks with great passion about Pinot Noir. After the release of this movie, sales of Pinot Noir wines rose by more than 20 percent over the 2004-05 Christmas/New Year period, compared to the same period the previous year. A similar phenomenon was experienced in British wine outlets. Miles is deeply disparaging, in a different scene, about Merlot, and sales dropped after the film came out. Ironically, Miles's prized bottle of wine, a 1961 Château Cheval Blanc, is a blend of Merlot and Cabernet Franc, another grape Miles disparaged.

This is the first film to win best screenplay from all five "major" critic groups (National Board Of Review, New York, Los Angeles, Broadcast and National Society Critics), the Golden Globes, the WGA and, ultimately, the Academy Awards.

The picture that Miles (Paul Giamatti) looks at when at his mother's home is actually a picture of Paul Giamatti and his father (former Yale University president and Commissioner of Major League Baseball) Bart Giamatti.

Thomas Haden Church had left film acting, concentrating on voiceover work, when he received a phone call from Alexander Payne to audition for the role of Jack. Church was a finalist for a role in About Schmidt (2002), another Payne film, and Payne wanted to use the actor in one of his films. Funnily enough, his character in the movie is also an actor who has retired from live-action performances to do voice-over work.

A slapstick scene involving Miles hitting a dog with his car while driving around was cut because it didn't fit the overall mood of the movie and didn't follow animal regulations that Hollywood had on using animals in movies.

Most of the wine used in the wine-tasting scenes was non-alcoholic. The actors wound up drinking so much of it that it made them nauseated (and had to periodically switch to the real thing to clean out their palates). Thomas Hayden Church estimated that grape juice or non-alcoholic wine was what they consumed 95 percent of the time. Conversely, Paul Giamatti claimed the actors drank real wine, and that he was actually very drunk after shooting a dinner scene.

Rex Pickett later produced a sequel in novel form named "Vertical", in which Miles writes a best seller and is again reunited with his mother and Jack. However according to Pickett, Alexander Payne had no interest in directing a film version of sequel.

When Miles and Jack are sitting on a car and Jack commiserates over the rejection of Miles' novel, Miles says "I'm a smudge of excrement on a tissue surging out to sea with a million tons of raw sewage," and Jack praises the phrasing, saying he (Jack) could never write anything like that. Miles then informs him that he couldn't write that either, and says he thinks it was a quote from Bukowski, referencing Charles ("Chuck") Bukowski. While the quote sounds like something Bukowski could have written, in fact it was written by the Sideways novel's author, and was never uttered by Bukowski.

An entire street was blocked off by the police for the filming of the scene in which M.C. Gainey runs naked down the street. Moreover, the people who lived in houses on said street were paid by the crew to stay inside their homes during the shooting of this particular scene.

Paul Giamatti admitted to faking every bit of wine knowledge, and not understanding why anybody would care about it. He also claims he was shocked that he was cast in a lead role and initially thought it was a practical joke.

According to W. Blake Gray of the San Francisco Chronicle, the producers had originally wanted to use a bottle of Petrus as the treasured wine gathering dust in Miles' apartment. But Christian Moueix, the chateau's owner, read the script and decided to pass. So, instead it was a bottle of 1961 Cheval Blanc.

Alexander Payne was flying back from Edinburgh, where he had been at a film festival promoting Election (1999), when he finally had a chance to read Rex Pickett's book Sideways. As soon as he landed, Payne ran to a pay phone to call his agent about purchasing the rights. He later told Pickett he liked his novel because his characters were "so f*cking pathetic."

Thomas Hayden Church was nervous about filming the love scene with Sandra Oh, as she was married to Alexander Payne at the time. Initially Church and Oh played the scene as if it was funny, before Payne made the two act more and more passionate with each successive take. Payne and Oh divorced two years later.

A reporter asked Alexander Payne if Miles running down the grassy hill was purposely evoking the opening credits to Little House on the Prairie (1974). It was actually borrowed, with permission, from the thesis film of one of Payne's former classmates.

Alexander Payne and Jim Taylor wrote Maya's speech based off of a passage from Rex Pickett's book, and based some of it on how the director himself feels about wine. However, he didn't think the speech deserved as much praise as it received.

During the opening credits, Miles drives west along Sunset Boulevard crossing the 405 freeway, indicating that the Erganians' house is located in the posh L.A. neighborhood of either Brentwood or Pacific Palisades.

Both of the New York Times crossword puzzles that Miles solves in the movie are actual published puzzles. The constructor's byline on the second puzzle Miles solves is visible; the puzzle was constructed by Alan Arbesfeld, and was published in the Times on 9 October 2003. The constructor's byline on the first puzzle (the one Miles solves while driving) is not visible; this puzzle was constructed by Craig Kasper and was published in the Times on 27 September 2003.

A scene where Miles runs over a dog was cut, even though Paul Giamatti's facial expressions in the scene made it supposedly funnier than it sounded. Scenes where an agitated Jack calls his fiancée during his trip were also taken out.

"The Sideways Wine Club", the licensee of Fox Searchlight Pictures, was started in April of 2005 and became the fastest growing wine club in the United States. It originally featured many of the wines seen in the movie then expanded to include similar wines from all over the world - wine from boutique producers who pour their heart and soul and second mortgage into their venture. Although the "Sideways" license has expired the Club continues to operate at

Some of the scenes in the novel were cut from the film version including the boar hunt, the trip to Hearst Castle, and the hot tub scene. Some of the characters and other plot points were also changed.

The house where Miles retrieved Jack's wallet was being used as a meth lab up until a few weeks before filming, when it was busted by police. Its interior was left essentially as is because the location scouts thought it was perfect for the scene.

When Miles is driving north from San Diego to meet Jack in West Los Angeles, it is presumed to be around 11 AM or Noon. However, when he is going through the Camp Pendleton stretch, it is clearly late afternoon based on the glow of the setting sun to the West and the shadows next to Miles' Saab. When he arrives in LA it is still mid-day.

Cameo

Rex Pickett: When Miles hits the ball back at the golfers behind them, the person who actually hit the ball was the author of the novel the film was based on. He claims that Paul Giamatti's exceptionally poor golf form made it impossible for him to accomplish the shot.

Spoilers

The trivia items below may give away important plot points.

Alexander Payne changed the ending of the book, because he thought it was "too Hollywood". In the book, Maya showed up at Jack's wedding to say she sees Miles in a more positive light after reading his manuscript.